NP-MRD: Showing NP-Card for (-)-Frullanolide (NP0051899)

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Record Information

Version

2.0

Created at

2022-04-27 23:06:10 UTC

Updated at

2022-04-27 23:06:10 UTC

NP-MRD ID

NP0051899

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Frullanolide

Description

Frullanolide belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. (-)-Frullanolide is found in Frullania dilatata, Frullania nisquallensis and Frullania tamarisci. (-)-Frullanolide was first documented in 2003 (PMID: 12755731). Based on a literature review a significant number of articles have been published on Frullanolide (PMID: 33901737) (PMID: 31186745) (PMID: 26594744) (PMID: 23484913) (PMID: 23023564).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    4.3827   -0.5548    0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2181    0.0268    0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000    1.2161   -0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8934    2.0234   -1.0967 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6295    1.2857   -0.8797 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0058    0.8204    0.3047 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4123    0.4730    0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3007    1.4613    0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8522    2.8787    0.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7582    1.2880    0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2260   -0.0969   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3031   -1.1130    0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8930   -0.9141   -0.1310 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8272   -1.3116   -1.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0093   -1.8840    0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4020   -1.6610    0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8762   -0.3589    0.6605 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2773   -0.1645   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4048   -1.4403    0.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1401    1.5536    1.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4461    3.5157   -0.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0781    3.1931    1.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1995    3.0366    0.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2913    1.7343    0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0551    1.9241   -0.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2201   -0.2256    0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4171   -0.2564   -1.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3494   -0.9777    1.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6168   -2.1262    0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7770   -1.1438   -2.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6737   -2.4264   -1.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0460   -0.7706   -2.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3238   -2.9193    0.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0098   -1.5746    1.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4170   -1.6014   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0895   -2.4463    0.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9307   -0.4634    1.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 17  1  0
 17 16  1  0
 16 15  1  0
 15 13  1  0
 13 14  1  6
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
 13  7  1  0
 17  6  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
  6 20  1  1
  1 18  1  0
  1 19  1  0
 17 37  1  1
 16 35  1  0
 16 36  1  0
 15 33  1  0
 15 34  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 12 28  1  0
 12 29  1  0
 11 26  1  0
 11 27  1  0
 10 24  1  0
 10 25  1  0
M  END


  Mrv1652304282201062D          

 17 19  0  0  1  0            999 V2000
    5.1704    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989    1.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608   -0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8307   -0.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3012   -1.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658    1.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  9 14  1  1  0  0  0
 14 15  2  0  0  0  0
  5 16  1  1  0  0  0
  3 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051899

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2[C@@H]3OC(=O)C(=C)[C@@H]3CC[C@@]2(C)CCC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O2/c1-9-5-4-7-15(3)8-6-11-10(2)14(16)17-13(11)12(9)15/h11,13H,2,4-8H2,1,3H3/t11-,13+,15+/m0/s1

> <INCHI_KEY>
PJPHIAMRKUNVSU-NJZAAPMLSA-N

> <FORMULA>
C15H20O2

> <MOLECULAR_WEIGHT>
232.323

> <EXACT_MASS>
232.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.141662577528905

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,5aR,9bR)-5a,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9bH-naphtho[1,2-b]furan-2-one

> <ALOGPS_LOGP>
3.95

> <JCHEM_LOGP>
3.4122912870000004

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.875320590275826

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
66.8493

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
frullanolide

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.651   0.722   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.923   2.079   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.384   2.127   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.573   0.818   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.301  -0.539   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.840  -0.587   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.490  -1.848   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.950  -1.800   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.222  -0.443   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.034   0.866   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.039   2.042   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.614   1.460   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.305   2.271   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.727  -0.076   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.551  -1.070   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.029  -1.896   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.656   3.484   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   16                                             
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    9   15                                                  
CONECT   15   14                                                            
CONECT   16    5                                                            
CONECT   17    3                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₂

Average Mass

232.3230 Da

Monoisotopic Mass

232.14633 Da

IUPAC Name

(3aS,5aR,9bR)-5a,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9bH-naphtho[1,2-b]furan-2-one

Traditional Name

frullanolide

CAS Registry Number

Not Available

SMILES

CC1=C2[C@@H]3OC(=O)C(=C)[C@@H]3CC[C@@]2(C)CCC1

InChI Identifier

InChI=1S/C15H20O2/c1-9-5-4-7-15(3)8-6-11-10(2)14(16)17-13(11)12(9)15/h11,13H,2,4-8H2,1,3H3/t11-,13+,15+/m0/s1

InChI Key

PJPHIAMRKUNVSU-NJZAAPMLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Frullania dilatata	Plant	KNApSAcK
Frullania nisquallensis	LOTUS Database	35616633
Frullania tamarisci	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

sesquiterpenoid (CHEBI:5177 )
Eudesmanes (C09454 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.95	ALOGPS
logP	3.41	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.85 m³·mol⁻¹	ChemAxon
Polarizability	26.14 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003287

Chemspider ID

141917

KEGG Compound ID

C09454

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

161573

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1384191

References

General References

Pathak S, Gokhroo A, Kumar Dubey A, Majumdar S, Gupta S, Almeida A, Mahajan GB, Kate A, Mishra P, Sharma R, Kumar S, Vishwakarma R, Balakrishnan A, Atreya H, Nandi D: 7-Hydroxy Frullanolide, a sesquiterpene lactone, increases intracellular calcium amounts, lowers CD4(+) T cell and macrophage responses, and ameliorates DSS-induced colitis. Int Immunopharmacol. 2021 Aug;97:107655. doi: 10.1016/j.intimp.2021.107655. Epub 2021 Apr 24. [PubMed:33901737 ]
Chimplee S, Graidist P, Srisawat T, Sukrong S, Bissanum R, Kanokwiroon K: Anti-breast cancer potential of frullanolide from Grangea maderaspatana plant by inducing apoptosis. Oncol Lett. 2019 Jun;17(6):5283-5291. doi: 10.3892/ol.2019.10209. Epub 2019 Apr 3. [PubMed:31186745 ]
Couleric P, Thouvenot L, Nour M, Asakawa Y: Chemical Originalities of New Caledonian Liverworts from Lejeuneaceae Family. Nat Prod Commun. 2015 Sep;10(9):1501-4. [PubMed:26594744 ]
Chou YY, Liao CC: First asymmetric total syntheses and determination of absolute configurations of (+)-eudesmadiene-12,6-olide and (+)-frullanolide. Org Lett. 2013 Apr 5;15(7):1584-7. doi: 10.1021/ol4003724. Epub 2013 Mar 13. [PubMed:23484913 ]
Patel MB, Amin D: Sphaeranthus indicus flower derived constituents exhibits synergistic effect against acetylcholinesterase and possess potential antiamnestic activity. J Complement Integr Med. 2012 Sep 24;9:Article 23. doi: 10.1515/1553-3840.1618. [PubMed:23023564 ]
Ducombs G, Lepoittevin JP, Berl V, Andersen KE, Brandao FM, Bruynzeel DP, Bruze M, Camarasa JG, Frosch PJ, Goossens A, Lachapelle JM, Lahti A, Le Coz CJ, Maibach HI, Menne T, Seidenari S, Shaw S, Tosti A, Wilkinson JD: Routine patch testing with frullanolide mix: an European Environmental and Contact Dermatitis Research Group multicentre study. Contact Dermatitis. 2003 Mar;48(3):158-61. doi: 10.1034/j.1600-0536.2003.00077.x. [PubMed:12755731 ]

Showing NP-Card for (-)-Frullanolide (NP0051899)

MOL for NP0051899 ((-)-Frullanolide)

3D MOL for NP0051899 ((-)-Frullanolide)

3D SDF for NP0051899 ((-)-Frullanolide)

3D-SDF for NP0051899 ((-)-Frullanolide)

PDB for NP0051899 ((-)-Frullanolide)

3D PDB for NP0051899 ((-)-Frullanolide)

SMILES for NP0051899 ((-)-Frullanolide)

INCHI for NP0051899 ((-)-Frullanolide)

Structure for NP0051899 ((-)-Frullanolide)

3D Structure for NP0051899 ((-)-Frullanolide)